Chat & Learn

Beyond the Pilot: How to Lead an AI Transformation That Sticks

5 speakers

October 14, 2026 2:00 – 3:00 PM ET Virtual Free to attend

Beyond the Pilot: How to Lead an AI Transformation That Sticks

About this session

Most AI initiatives don’t fail because of the technology. They fail because companies underestimate how much the right people, in the right roles, with the right implementation support around them, actually matter. In this session, leaders from across industries will share what separates organizations that scale AI successfully from those that don’t, including real examples of transformations that built lasting internal capability and left teams confident enough to own the work themselves.

Topics will include:

AI initiatives stall on people and process, not technology. The organizations that scale successfully are the ones that invest as much in the right roles and implementation support as they do in the model itself, because that's usually where the gap actually shows up.
Scaling AI means building internal capability, not just running a pilot. The difference between a one-off proof of concept and a lasting transformation comes down to whether teams develop the skills and ownership to carry the work forward on their own.
Confidence is the real marker of success. The organizations that get AI transformation right leave their teams feeling equipped and trusted to own the work themselves, rather than dependent on outside support to keep it running.

This event will be eligible for SHRM credits.

Meet the speakers

Hunter Lee Canning

Founder of Plumwheel & PowerToFly Virtual Event Host

Hunter Lee Canning (he/they) is allergic to corporate jargon and proud of it. With two decades in Hollywood and over 800 virtual events hosted, Hunter delivers no-BS keynotes showing B2B teams how to break free from boring 'professional' presentations. As the queer, neurodiverse founder of Plumwheel, Hunter has perfected this approach by turning conversations into compelling video campaigns that boost engagement 300% for growing companies and enterprises. Sales teams love them, CFOs fund them. Go figure. You can connect with Hunter on LinkedIn.

Eryn Peters

Co-Creator @ AI Maturity Index

Eryn is a future of work evangelist, retired digital nomad, workforce expert, and scale-up builder. She is the founder of Startup Consortium, editor of Weekly Workforce, and Co-Creator of the AI Maturity Index. Before founding Startup Consortium, she built two unicorns in the staffing industry where her work has helped 4.5 million people in over 190 countries access new learning and job opportunities.

Ken Sterling

AI, Tech and Media Attorney, Sterling Media Law and Opus Intelligence Labs

Ken Sterling is not a lawyer who learned technology from the sidelines. He has been coding since 8th grade, worked at Intel, earned Cisco CCNA, Microsoft MCSE, and CompTIA A+ certifications, and built data centers before becoming a lawyer. Today, Ken is a Century City technology, AI, media, and business attorney, VC LP, entrepreneur, USC professor, and board advisor with a rare blend of legal, technology, media, and operating experience. He co-founded an early cloud CRM company that was partially acquired by KPMG, then co-founded a bank, and in his earlier years, co-founded a global manufacturing company. Ken serves as general counsel and strategic advisor to technology and growth companies, advising founders, executives, investors, platforms, and media businesses on law, capital, AI, data, intellectual property, transactions, reputation, platform liability, and business strategy. He teaches at USC Gould School of Law and USC Annenberg, serves as General Counsel to Opus Intelligence Labs, and writes as a columnist for Forbes and Inc. Magazine.

Kelly Blackmon

Founder of B.E. Consulting

Kelly Blackmon is an organizational strategist and founder of B.E. Consulting. His work focuses on culture architecture, AI integration, and leadership decision-making under acceleration. Through frameworks like AI-EQ and CultureEQ, he helps organizations assess stability, clarify risk exposure, and implement transformation without eroding trust or performance. Kelly has advised leaders across HR, talent, and executive functions on aligning innovation with workforce integrity.

Stephen Salaka

AI Enablement Manager, HII Mission Technologies

Stephen Salaka leads AI Enablement for HII Mission Technologies, where he runs the AI and custom-agent teams and the governance program that puts AI tools in the hands of more than 8,000 users across the division. He came to the work sideways. Thirty years of building and merging technology organizations (12 post-acquisition IT groups folded into one at SMTC, predictive maintenance software for the F-35 and F-22 before that) taught him that the technology is rarely what fails. People do, when nobody plans for them. That pushed him into pursuing his PhD in industrial/organizational psychology, and it is the lens he brings to AI adoption now: why pilots stall, what makes a new habit survive contact with a real workday, and how leaders can tell the difference between a rollout and a transformation. He also holds an MBA and a BS in computer science, and has spent six years working in Japan, which is where he first learned that a change plan nobody believes in is worse than cat herding. cats

Register for this session

Registration

About PowerToFly

The bridge between professionals and the companies building what's next.

PowerToFly connects talent, community groups, and industry leaders in one platform. Meet hiring managers, recruiters, and peers from anywhere — and with our virtual events and exclusive career content, hone your skills and grow your network all in one place.

Community

800K+ Active members across every industry, domain, and geography — from anywhere in the world.

Verified experts

80K+ Domain specialists in healthcare, law, finance, and more — vetted and ready.

AI professionals

6,500 Annotators, red teamers, and model evaluators who've worked on frontier AI.

Countries

204 A truly global community, so you can connect and grow your network without borders.

Women & BIPOC

75%+ The voices most underrepresented in tech are overrepresented here — by design.

Years building

12+ Connecting talent with companies that value it, since 2014.

More Chat & Learns

See all events →

October 14, 2026

For employers

From Data to Deployment: Why the Humans Behind Your Model Determine Its ROI

Your AI model is only as good as the people shaping it. That means bringing in experts with varied backgrounds, industries, and lived experiences, because that breadth is what produces outputs that reflect the world your customers actually live in. In this deep dive, we’ll talk about what it takes to train, evaluate,…

5 speakers

October 14, 2026

For employers

The Hiring Gap: Why Most Companies Are Looking for AI Talent in All the Wrong Places

Finding great AI talent isn’t just about technical skills anymore, and the companies figuring that out are moving faster than everyone else. They’re looking for people who already understand their industry and can bring real-world context. Join us to learn what smarter sourcing looks like these days and why…

5 speakers

October 6, 2026

For employers

What Comes Next: Retaining and Advancing Women Leaders Now

Building and retaining diverse, high-performing teams has always been important. But in today’s post-DEI, multi-generational workplace, with the expansion of (and uncertainties around) AI, it's even more important - and more challenging. Join us as we speak with the workplace experts from Prepare to Launch who will…

2 speakers

Watch recording →

Save your spot

Bring your questions.

It's free, it's virtual, and it's built for a real conversation — not a lecture. Register to join live, or to get the recording afterward.